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EP0061579B1 - Flavor stable and shelf stable citrus oil concentrate - Google Patents

Flavor stable and shelf stable citrus oil concentrate Download PDF

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Publication number
EP0061579B1
EP0061579B1 EP82101277A EP82101277A EP0061579B1 EP 0061579 B1 EP0061579 B1 EP 0061579B1 EP 82101277 A EP82101277 A EP 82101277A EP 82101277 A EP82101277 A EP 82101277A EP 0061579 B1 EP0061579 B1 EP 0061579B1
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Prior art keywords
concentrate
citrus
peel oil
oil
weight
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German (de)
French (fr)
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EP0061579A1 (en
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Erich Ziegler
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    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/70—Fixation, conservation, or encapsulation of flavouring agents

Definitions

  • the invention relates to concentrates from natural citrus oils which are used to improve the taste of natural fruit juices from citrus fruits and also from lemonades.
  • thermolabile substances which have to be regarded as carriers of the desired aroma nuances.
  • the thermolability of the raw materials means that they only have to be stored in the deep-freeze state and must also be delivered to the consumer, i.e. generally to the beverage manufacturer, via freezer chains. This necessity is technically complex and increases the cost of the drinks considerably.
  • the invention has for its object to produce a storage-stable citrus flavor concentrate, which does not change or lose its aroma even in prolonged storage (a few weeks to several months) at room temperature in both pure and diluted form.
  • the solution to this problem results from patent claim 1.
  • the invention is based on the observation that substances are contained in the peel oil which act as stabilizers.
  • the substances can be enriched using suitable processes and the peel oil concentrate obtained in this way can be used as a stabilizing agent for natural citrus flavor concentrates.
  • a preferred composition of the storage-stable citrus aroma concentrate proposed according to the invention for improving the taste of natural fruit juices from citrus fruits and of lemonades consists of 10 to 90% by weight of citrus peel oil concentrate and 90 to 10% by weight of essential oil concentrate. Another preferred composition consists of 10 to 95% by weight of citrus peel oil concentrate, the remainder concentrate of aqueous essence. Another preferred composition consists of 10 to 90% by weight of citrus peel oil concentrate, 5 to 85% by weight of essence oil concentrate and 5 to 85% by weight concentrate from aqueous essence.
  • the production of the peel oil concentrate is essential for the storage stability of the specified citrus oil concentrate.
  • the inventor has observed that the substances mentioned which act as stabilizers can be obtained from the citrus peel oil concentrate or enriched therein if the cold-pressed citrus peel oil is passed in a chromatographic column over such solid separating agents which adsorb polar organic substances. Active silica gel has proven to be particularly suitable; however, other corresponding release agents can also be used, for example finely divided aluminum oxide.
  • the separating agent is washed with a little non-polar solvent, for example petroleum ether, and then the adsorbed fraction is eluted with a polar organic substance, for example ethanol.
  • the recovered adsorbed fraction can be separated from the eluate with saturated saline.
  • Adsorption in the chromatographic separation column has proven to be the most effective. However, it is also possible to enrich the desired substances by extraction with polar organic solvents. “Polar organic solvents” are understood to mean chemically uniform substances as well as mixtures of several polar organic solvents. Ethanol has proven to be particularly suitable for carrying out this process.
  • the substances mentioned here namely tocopherols, carotenoids, lipoids, phosphorus lipids and similar groups of substances, are enriched by the methods mentioned. Unwanted labile compounds of the citrus products, such as monoterpenes and sesquiterpenes, are largely separated.
  • a glass tube with a diameter of 13 mm and a length of 1000 mm was filled with 35 g of active silica gel.
  • 200 cold-pressed California orange oil were passed through the separation column prepared in this way. After the oil had passed through, it was washed with 50 ml of petroleum ether and then eluted with 150 ml of concentrated ethanol (96% by volume).
  • the oil was insoluble in 96% ethanol.
  • Solubility Clearly soluble in orange peel oil and water.
  • the concentrates have a strong flavor. 5-10 g of the concentrate mixture is sufficient for the flavoring of 100 lemonade.
  • Tocopheroi test was used to demonstrate the shelf life.
  • Tocopherol vitamin E
  • Tocopherol can be determined by thin layer chromatography. High-resolution thin-layer chromatography plates from Merck Darmstadt were used to carry out the comparison test chosen here.

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  • Health & Medical Sciences (AREA)
  • Nutrition Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Seasonings (AREA)
  • Fats And Perfumes (AREA)

Description

Die Erfindung betrifft Konzentrate aus natürlichen Zitrusölen, die zur Geschmacksverbesserung von Natur-Fruchtsäften aus Zitrusfrüchten sowie auch von Limonaden verwendet werden.The invention relates to concentrates from natural citrus oils which are used to improve the taste of natural fruit juices from citrus fruits and also from lemonades.

Aus der natürlichen Frucht stammende Stoffe, die als Aromaträger bei den genannten Einsatzgebieten in Betracht kommen, fallen bei der Aufarbeitung der meist frisch geernteten Früchte zunächst als Schalenöl, Essenzöl sowie als wässrige Essenz an. Die Stoffe werden alsdann weiter konzentriert, um ihren Aromagehalt zu erhöhen sowie um unerwünschte Stoffe abzuscheiden. Die Rohstoffe sind komplizierte Gemische aus teils sehr thermolabilen Stoffen, welche als Träger der erwünschten Aromanuancen angesehen werden müssen. Die Thermolabilität der Rohstoffe bringt es mit sich, dass diese nur im tiefgekühlten Zustand gelagert und auch über Tiefkühlketten vom Hersteller an den Verbraucher, also in der Regel den Getränkehersteller geliefert werden müssen. Diese Notwendigkeit ist technisch aufwendig und verteuert die Getränke erheblich.Substances derived from the natural fruit, which come into consideration as aroma carriers in the fields of application mentioned, are initially obtained when processing the mostly freshly harvested fruits as peel oil, essential oil and as an aqueous essence. The substances are then further concentrated in order to increase their aroma content and to separate out undesirable substances. The raw materials are complex mixtures of sometimes very thermolabile substances, which have to be regarded as carriers of the desired aroma nuances. The thermolability of the raw materials means that they only have to be stored in the deep-freeze state and must also be delivered to the consumer, i.e. generally to the beverage manufacturer, via freezer chains. This necessity is technically complex and increases the cost of the drinks considerably.

Der Erfindung liegt die Aufgabe zugrunde, ein lagerbeständiges Zitrusaroma-Konzentrat herzustellen, welches auch bei längerer Lagerung (einige Wochen bis mehrere Monate) bei Raumtemperatur sowohl in reiner wie auch in verdünnter Form sein Aroma nicht verändert oder verliert. Die Lösung dieser Aufgabe ergibt sich aus Patentanspruch 1.The invention has for its object to produce a storage-stable citrus flavor concentrate, which does not change or lose its aroma even in prolonged storage (a few weeks to several months) at room temperature in both pure and diluted form. The solution to this problem results from patent claim 1.

Die Erfindung beruht auf der Beobachtung, dass im Schalenöl Stoffe enthalten sind, die als Stabilisatoren wirken. Die Stoffe können mit Hilfe geeigneter Verfahren angereichert und das so gewonnene Schalenöl-Konzentrat als Stabilisierungsmittel für natürliche Zitrusaroma-Konzentrate verwendet werden.The invention is based on the observation that substances are contained in the peel oil which act as stabilizers. The substances can be enriched using suitable processes and the peel oil concentrate obtained in this way can be used as a stabilizing agent for natural citrus flavor concentrates.

Zum leichteren Verständnis der Erfindung werden im folgenden einige Definitionen angeführt:

  • 1. Unter «Schalenöl» werden Öle verstanden, die durch Pressen der vom Fruchtfleisch befreiten Zitrusfruchtschalen auf kaltem Wege gewonnen werden.
  • 2. Unter «Essenzöl» wird die ölige Phase verstanden, welche beim Kondensieren der Brüden gewonnen wird, die beim Eindampfen von Zitrusfruchtsäften entweichen.
  • 3. Unter «wässriger Essenz» wird die wässrige Phase verstanden, die beim Kondensieren der Brüden anfällt, die beim Eindampfen der Zitrusfruchtsäfte entweichen.

Die hier angesprochene Problematik besteht generell bei allen Erzeugnissen aus Zitrusfrüchten, wozu also insbesondere Orangen, Zitronen, Mandarinen und Grapefrüchte zu rechnen sind.Some definitions are given below for easier understanding of the invention:
  • 1. “Peel oil” is understood to mean oils which are obtained by pressing the citrus fruit peels freed from the pulp in a cold way.
  • 2. “Essence oil” is understood to mean the oily phase which is obtained when the vapors condense, which escape when evaporating citrus fruit juices.
  • 3. “Aqueous essence” means the aqueous phase that occurs when the vapors condense, which escape when the citrus fruit juices are evaporated.

The problem addressed here generally consists of all products made from citrus fruits, which includes oranges, lemons, mandarins and grapefruits.

Eine bevorzugte Zusammensetzung des erfindungsgemäss vorgeschlagenen, lagerstabilen Zitrusaroma-Konzentrates zur Geschmacksverbesserung von Natur-Fruchtsäften aus Zitrusfrüchten sowie von Limonaden besteht aus 10 bis 90 Gew.% Zitrusschalenöl-Konzentrat und 90 bis 10 Gew.% Essenzöl-Konzentrat. Eine andere bevorzugte Zusammensetzung besteht aus 10 bis 95 Gew.% Zitrusschalenöl-Konzentrat, Rest Konzentrat aus wässriger Essenz. Eine weitere bevorzugte Zusammensetzung besteht aus 10 bis 90 Gew.% Zitrusschalenöl-Konzentrat, 5 bis 85 Gew.% Essenzöl-Konzentrat und 5 bis 85 Gew.% Konzentrat aus wässriger Essenz.A preferred composition of the storage-stable citrus aroma concentrate proposed according to the invention for improving the taste of natural fruit juices from citrus fruits and of lemonades consists of 10 to 90% by weight of citrus peel oil concentrate and 90 to 10% by weight of essential oil concentrate. Another preferred composition consists of 10 to 95% by weight of citrus peel oil concentrate, the remainder concentrate of aqueous essence. Another preferred composition consists of 10 to 90% by weight of citrus peel oil concentrate, 5 to 85% by weight of essence oil concentrate and 5 to 85% by weight concentrate from aqueous essence.

Wesentlich für die Lagerstabilität des angegebenen Zitrusöl-Konzentrates ist die Herstellung des Schalenölkonzentrates. Der Erfinder hat beobachtet, dass die erwähnten als Stabilisatoren wirkenden Stoffe aus dem Zitrusschalenöl-Konzentrat gewonnen bzw. in diesem angereichert werden können, wenn das kaltgepresste Zitrusschalenöl in einer chromatografischen Säule über solche feste Trennmittel geleitet wird, die polare organische Stoffe adsorbieren. Als besonders geeignet hat sich aktives Kieselgel erwiesen; es sind aber auch andere entsprechend wirkende Trennmittel brauchbar, beispielsweise fein verteiltes Aluminiumoxid. Nach dem Überleiten des Ausgangsöles wird das Trennmittel mit wenig unpolarem Lösungsmittel, beispielsweise Petroläther, nachgewaschen und dann die adsorbierte Fraktion mit einem polaren organischen Stoff, beispielsweise Ethanol eluiert. Aus dem Eluat kann die zurückgewonnene adsorbierte Fraktion mit gesättigter Kochsalzlösung ausgeschieden werden.The production of the peel oil concentrate is essential for the storage stability of the specified citrus oil concentrate. The inventor has observed that the substances mentioned which act as stabilizers can be obtained from the citrus peel oil concentrate or enriched therein if the cold-pressed citrus peel oil is passed in a chromatographic column over such solid separating agents which adsorb polar organic substances. Active silica gel has proven to be particularly suitable; however, other corresponding release agents can also be used, for example finely divided aluminum oxide. After the starting oil has been passed over, the separating agent is washed with a little non-polar solvent, for example petroleum ether, and then the adsorbed fraction is eluted with a polar organic substance, for example ethanol. The recovered adsorbed fraction can be separated from the eluate with saturated saline.

Die Adsorption in der chromatografischen Trennsäule hat sich am wirkungsvollsten erwiesen. Es ist aber auch möglich, die gewünschten Stoffe durch Extraktion mit polaren organischen Lösungsmitteln anzureichern. Unter «polaren organischen Lösungsmitteln» werden chemisch einheitliche Stoffe aber auch Gemische aus mehreren polaren organischen Lösungsmitteln verstanden. Als besonders geeignet für die Durchführung dieses Verfahrens hat sich Ethanol erwiesen.Adsorption in the chromatographic separation column has proven to be the most effective. However, it is also possible to enrich the desired substances by extraction with polar organic solvents. “Polar organic solvents” are understood to mean chemically uniform substances as well as mixtures of several polar organic solvents. Ethanol has proven to be particularly suitable for carrying out this process.

Durch die erwähnten Methoden werden die hier in Betracht kommenden Stoffe, nämlich Tocopherole, Carotinoide, Lipoide, Phosphorlipide und ähnliche Stoffgruppen angereichert. Unerwünschte labile Verbindungen der Zitrusprodukte, wie Monoterpene und Sesquiterpene werden weitgehend abgeschieden.The substances mentioned here, namely tocopherols, carotenoids, lipoids, phosphorus lipids and similar groups of substances, are enriched by the methods mentioned. Unwanted labile compounds of the citrus products, such as monoterpenes and sesquiterpenes, are largely separated.

Die Erfindung wird im folgenden anhand einiger Beispiele erläutert:The invention is illustrated below with the aid of a few examples:

Beispiel 1example 1

Gewinnung von lagerstabilem und konservierend wirkendem Orangen-SchalenölkonzentratObtaining orange peel oil concentrate that is stable in storage and has a preservative effect

Ein Glasrohr mit 13 mm Durchmesser und 1000 mm Länge wurde mit 35 g aktivem Kieselgel gefüllt. Durch die so vorbereitete Trennsäule wurden 200 kalt gepresstes kalifornisches Orangenöl geleitet. Nach dem Durchlauf des Öles wurde mit 50 ml Petroläther nachgewaschen und danach mit 150 ml konzentriertem Ethanol (96 Vol%) eluiert.A glass tube with a diameter of 13 mm and a length of 1000 mm was filled with 35 g of active silica gel. 200 cold-pressed California orange oil were passed through the separation column prepared in this way. After the oil had passed through, it was washed with 50 ml of petroleum ether and then eluted with 150 ml of concentrated ethanol (96% by volume).

Das gewonnene Eluat wurde in 500 ml gesättigte Kochsalzlösung eingegossen, wobei sich ein Öl abschied. Nach dem Absetzen wurden die Phasen getrennt und es wurden ca. 5 g konzentriertes Orangenöl erhalten.

  • Daten: D 20°C = 0,913 g/cm3
  • nD20°C = 1,478
The eluate obtained was poured into 500 ml of saturated saline, whereby a Oil goodbye. After settling, the phases were separated and about 5 g of concentrated orange oil were obtained.
  • Data: D 20 ° C = 0, 913 g / cm3
  • n D 20 ° C = 1.478

Zusammensetzung:

  • 31,8% Aldehyd, berechnet als Dezylaldehyd
  • 0,9% Säure berechnet als Essigsäure
  • 16,6% Ester berechnet als Geranylazetat
  • 18,2% Alkohol berechnet als Linalool.

Das gewonnene Konzentrat war in 96%igem Ethanol unlöslich.Composition:
  • 31.8% aldehyde, calculated as decyl aldehyde
  • 0.9% acid calculated as acetic acid
  • 16.6% ester calculated as geranyl acetate
  • 18.2% alcohol calculated as linalool.

The concentrate obtained was insoluble in 96% ethanol.

Beispiel 2Example 2

Gewinnung von lagerstabilem und konservierend wirkendem Grapefrucht-Schalenölkonzentrat Ein Glasrohr mit 13 mm Durchmesser und 1000 mm Länge wurde mit 35 g aktivem Kieselgel gefüllt. Durch das so vorbereitete Adsorptionsrohr wurden 200 g kaltgepresstes Grapefruchtöl geleitet und nach dessen Durchlauf mit 50 ml Petroläther nachgewaschen. Nach Ablauf des Petroläthers wurde mit 150 ml Ethanol (96 Vol.%) eluiert. Das Eluat wurde aufgefangen und der Ethanol unter vermindertem Druck abdestilliert (Druck etwa 20 mbar). Als Rückstand wurden ca. 5 g Grapefruchtöl-Konzentrat erhalten.

  • Daten: D 20°C = 1,017 g/cm3
  • nD20°C = 1,52
Obtaining storage-stable and preserving grapefruit peel oil concentrate A glass tube with a diameter of 13 mm and a length of 1000 mm was filled with 35 g of active silica gel. 200 g of cold-pressed grapefruit oil were passed through the adsorption tube prepared in this way and, after passing through it, washed with 50 ml of petroleum ether. After the petroleum ether had eluted, it was eluted with 150 ml of ethanol (96% by volume). The eluate was collected and the ethanol was distilled off under reduced pressure (pressure about 20 mbar). About 5 g of grapefruit oil concentrate were obtained as a residue.
  • Data: D 20 ° C = 1.017 g / cm 3
  • n D 20 ° C = 1.52

Das Öl war unlöslich in 96%igem Ethanol.The oil was insoluble in 96% ethanol.

Beispiel 3Example 3

Gewinnung von lagerstabilem und konservierend wirkendem Zitronen-Schalenölkonzentrat In einem Scheidetrichter mit 500 ml Inhalt wurden 200g Zitronenschalenöl eingefüllt. Das Öl wurde viermal mit je 100 ml Ethanol (73 Gew.%) ausgeschüttelt und die Alkoholphase abgetrennt. Die vereinigten Alkoholphasen wurden in 800 ml gesättigte Kochsalzlösung eingerührt, wobei sich ein Öl abschied. Nach dem Absetzen des Öles und Waschen mit zweimal 50 ml Wasser wurde 22 g Konzentrat gewonnen.

  • Daten: D 20°C = 0,860
  • nD20°C= 1,477
Obtaining Lemon-Peel Oil Concentrate that Stages and Preserves Storage 200 g of lemon-peel oil were poured into a separating funnel with a volume of 500 ml. The oil was extracted four times with 100 ml of ethanol (73% by weight) and the alcohol phase was separated. The combined alcohol phases were stirred into 800 ml of saturated saline, an oil separating out. After the oil had settled and washed with twice 50 ml of water, 22 g of concentrate were obtained.
  • Data: D 20 ° C = 0.860
  • n D 20 ° C = 1.477

Löslichkeit in 90%igem Ethanol 1:3.Solubility in 90% ethanol 1: 3.

Zusammensetzung:

  • 12,7% Aldehyd berechnet als Dezylaldehyd
  • 0,15% Säure berechnet als Essigsäure
  • 5,8% Ester berechnet als Geranylazetat
Composition:
  • 12.7% aldehyde calculated as decyl aldehyde
  • 0.15% acid calculated as acetic acid
  • 5.8% ester calculated as geranyl acetate

Beispiel 4Example 4

Gewinnung eines Orangen-Essenzölkonzentrates In einen Scheidetrichter mit 200 ml Inhalt wurden 100 Orangenessenzöl eingefüllt. Das Öl wurde viermal mit je 50 ml Ethanol (62 Gew.%) ausgeschüttelt und die Alkoholphase abgetrennt. Die vereinigten Extrakte wurden in 500 ml gesättigte Kochsalzlösung eingerührt, wobei sich ein Öl abschied. Nach dem Absetzen des Öles wurde dieses in bekannter Weise gewonnen. Ausbeute: 6 g.

  • Daten: D 20°C = 0,857 g/cm3
  • nD20°C = 1,476
Obtaining an Orange Essence Oil Concentrate 100 orange essence oils were placed in a separating funnel with a volume of 200 ml. The oil was extracted four times with 50 ml of ethanol (62% by weight) and the alcohol phase was separated. The combined extracts were stirred into 500 ml of saturated saline, an oil separating out. After the oil had settled, it was obtained in a known manner. Yield: 6 g.
  • Data: D 20 ° C = 0.857 g / cm3
  • n D 20 ° C = 1.476

Löslichkeit in 90%igem Ethanol 1:1. Zusammensetzung:

  • 12,2% Aldehyd berechnet als Dezylaldehyd
  • 0,1% Säure berechnet als Essigsäure,
  • 5,7% Ester berechnet als Geranylazetat
Solubility in 90% ethanol 1: 1. Composition:
  • 12.2% aldehyde calculated as decyl aldehyde
  • 0.1% acidity calculated as acetic acid,
  • 5.7% ester calculated as geranyl acetate

Beispiel 5Example 5

Gewinnung eines Grapefrucht-EssenzölkonzentratesObtaining a grapefruit essential oil concentrate

In eine Fraktionierapparatur, deren Kolbeninhalt 1000 ml betrug, und die einen Fraktionieraufsatz aufwies, wurden 500 g Grapefruchtessenzöl eingefüllt. Bei vermindertem Druck von 20 mbar und Kühlung der Vorlage mit flüssigem Stickstoff wurde die Destillation durch vorsichtige Temperaturerhöhung langsam eingeleitet. Nachdem 15 ml Destillat übergegangen waren, wurde die Destillation abgebrochen. Das Destillat stellte das gewünschte Konzentrat her. Es hatte folgende Daten:

  • D 20°C = 0,842
  • nD20°C= 1,4705
500 g of grapefruit essence oil were introduced into a fractionation apparatus, the flask content of which was 1000 ml, and which had a fractionation attachment. At a reduced pressure of 20 mbar and cooling the receiver with liquid nitrogen, the distillation was slowly initiated by carefully raising the temperature. After 15 ml of distillate had passed over, the distillation was stopped. The distillate produced the desired concentrate. It had the following data:
  • D 20 ° C = 0.842
  • nD20 ° C = 1.4705

Löslichkeit in 90%igem Ethnaol 1:6Solubility in 90% ethanol 1: 6

Zusammensetzung:

  • 3,17% Aldehyd berechnet als Dezylaldehyd
  • 0,02% Säure berechnet als Essigsäure
  • 3,0% Ester berechnet als Geranylazetat.
Composition:
  • 3.17% aldehyde calculated as decyl aldehyde
  • 0.02% acid calculated as acetic acid
  • 3.0% ester calculated as geranyl acetate.

Beispiel 6Example 6

Gewinnung eines Konzentrates aus wässriger OrangenessenzObtaining a concentrate from aqueous orange essence

In eine Fraktionierapparatur mit 1000 ml Kolbeninhalt und Fraktionieraufsatz wurde 500g wässrige Orangenessenz eingefüllt. Nach langsamem Abdestillieren der bis 85°C übergehenden Fraktion wurden 30 ml Destillat erhalten. Das Destillat war das gewünschte Konzentrat. Es hatte folgende Daten:

  • D 20°C = 0,813 g/cm3
  • nD20°C = 1,365
500 g of aqueous orange essence were introduced into a fractionation apparatus with a flask content of 1000 ml and a fractionation attachment. After slowly distilling off the fraction passing to 85 ° C., 30 ml of distillate were obtained. The distillate was the desired concentrate. It had the following data:
  • D 20 ° C = 0.813 g / cm 3
  • n D 20 ° C = 1.365

Löslichkeit: Klar löslich in Orangen-Schalenöl und Wasser.Solubility: Clearly soluble in orange peel oil and water.

Zusammensetzung:

  • 5,6% Aldehyd, berechnet als Dezylaldehyd
  • 0,02% Säure, berechnet als Essigsäure,
  • 0,46% Ester, berechnet als Geranylazetat

Erfindungsgemäss wird das gewonnene Schalenöl-Konzentrat nun je nach Bedarf mit Essenzöl-Konzentrat, dem Konzentrat der wässrigen Essenz oder beiden vermischt. Die einzusetzende Menge des Schalenöl-Konzentrates richtet sich nach dem Grad der gewünschten Stabilisierung sowie auch danach, ob der Geschmack der Fruchtschale hervorgehoben werden soll oder nicht.Composition:
  • 5.6% aldehyde, calculated as decyl aldehyde
  • 0.02% acid, calculated as acetic acid,
  • 0.46% ester, calculated as geranyl acetate

According to the invention, the shell oil concentrate obtained is now mixed with essence oil concentrate, the concentrate of the aqueous essence or both, as required. The amount of peel oil concentrate to be used depends on the degree of stabilization desired and also whether the taste of the fruit peel should be emphasized or not.

Die Konzentrate haben starkes Aromatisierungsvermögen. 5-10 g der Konzentratmischung ist ausreichend für die Aromatisierung von 100 Limonade.The concentrates have a strong flavor. 5-10 g of the concentrate mixture is sufficient for the flavoring of 100 lemonade.

Zur Demonstration der Haltbarkeit wurde der sogenannte «Tocopheroi-Test» herangezogen. Tocopherol (Vitamin E) ist bekanntlich eine äusserst thermolabile Substanz, welche in zahlreichen Früchten, so auch in Zitrusfrüchten vorkommt. Tocopherol kann durch Dünnschichtchromatografie bestimmt werden. Hochauflösende Dünnschichtchromatografie-Fertigplatten der Firma Merck Darmstadt wurden zur Durchführung des hier gewählten Vergleichstestes verwendet.The so-called "Tocopheroi test" was used to demonstrate the shelf life. Tocopherol (vitamin E) is known to be an extremely thermolabile substance, which is found in numerous fruits, including citrus fruits. Tocopherol can be determined by thin layer chromatography. High-resolution thin-layer chromatography plates from Merck Darmstadt were used to carry out the comparison test chosen here.

Zur Durchfühung des Testes wurden 20 ul der zu untersuchenden Substanz auf eine chromatografische hochauflösende Dünnschichtplatte aufgetragen. Als Fliessmittel wurde Chloroform in aufsteigender Phase verwendet. Nach Durchführung der Trennung wurde die Platte mit einer Lösung von einem Teil Antimonpentachlorid in vier Teilen Chloroform besprüht. Der Tocopherolfleck wurde dabei durch eine rotbraune Färbung sichtbar.

Figure imgb0001
To carry out the test, 20 μl of the substance to be examined was applied to a high-resolution chromatographic thin-layer plate. Chloroform in the ascending phase was used as the mobile phase. After the separation was carried out, the plate was sprayed with a solution of one part of antimony pentachloride in four parts of chloroform. The tocopherol stain was visible through a red-brown color.
Figure imgb0001

Claims (4)

1. Use of peel oil concentrate, prepared from cold-pressed citrus peel oil by adsorption on solid separating agents which adsorb polar organic substances or by extraction with polar liquid solvents, as a stabiliser for natural citrus flavour concentrates.
2. Citrus flavour concentrate, having a long shelf life, for improving the flavour of natural fruit juices obtained from citrus fruits and of soft drinks, which consists of 10 to 90% by weight of citrus peel oil concentrate, prepared from cold- presssed citrus peel oil by adsorption on solid separating agents which adsorb polar organic substances or by extraction with polar liquid solvents, and 90 to 10% by weight of an essential oil concentrate.
3. Citrus flavour concentrate, having a long shelf life, according to Claim 1, which consists of 10 to 95% by weight of citrus peel oil concentrate, prepared from cold-pressed citrus peel oil by adsorption on solid separating agents which adsorb polar organic substances or by extraction with polar liquid solvents, the remainder being a concentrate of aqueous essence.
4. Citrus flavour concentrate, having a long shelf life, according to Claim 1, which consists of 10 to 90% by weight of citrus peel oil concentrate, prepared from cold-pressed citrus peel oil by adsorption on solid separating agents which adsorb polar organic substances or by extraction with polar liquid solvents, 5 to 85% by weight of essential oil concentrate, and 5 to 85% by weight of a concentrate of aqueous essence.
EP82101277A 1981-03-28 1982-02-19 Flavor stable and shelf stable citrus oil concentrate Expired EP0061579B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3112380 1981-03-28
DE3112380A DE3112380C2 (en) 1981-03-28 1981-03-28 Storage-stable citrus fruit flavor concentrate

Publications (2)

Publication Number Publication Date
EP0061579A1 EP0061579A1 (en) 1982-10-06
EP0061579B1 true EP0061579B1 (en) 1984-07-11

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EP82101277A Expired EP0061579B1 (en) 1981-03-28 1982-02-19 Flavor stable and shelf stable citrus oil concentrate

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US (2) US4435437A (en)
EP (1) EP0061579B1 (en)
AU (2) AU558191B2 (en)
BR (1) BR8201730A (en)
DE (2) DE3112380C2 (en)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4952751A (en) * 1988-04-08 1990-08-28 Membrane Technology & Research, Inc. Treatment of evaporator condensates by pervaporation
US4941995A (en) * 1988-07-05 1990-07-17 Scott Paper Company Natural preservative composition for wet wipes
US4970085A (en) * 1989-10-19 1990-11-13 The Procter & Gamble Company Process for making improved citrus aqueous essence and product produced therefrom
US6495193B2 (en) * 1999-12-29 2002-12-17 Takasago International Corporation Citrus flavor having high stability, method of preparation thereof and food and drink product containing said flavor
WO2007100567A2 (en) * 2006-02-22 2007-09-07 Greger Douglas L Method and composition for improved meat quality
WO2010002696A1 (en) * 2008-06-30 2010-01-07 The Coca-Cola Company Essential oil processing
US8323513B2 (en) 2009-07-28 2012-12-04 Cp Kelco Aps Dewatering biomass material comprising polysaccharide, method for extracting polysaccharide from biomass material, and dewatered biomass material
US9499640B2 (en) 2011-01-21 2016-11-22 Cp Kelco Aps Preservation of biomass material comprising polysaccharide and method for extracting polysaccharide from preserved biomass material

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BE549252A (en) *
US2712008A (en) 1951-06-29 1955-06-28 Justus G Kirchner Production of terpeneless essential oils
US2754215A (en) * 1952-10-04 1956-07-10 American Maize Prod Co Method of stabilizing the flavor of essential oils and the resulting composition
US3294550A (en) * 1961-10-12 1966-12-27 Robert M Ikeda Production of full-flavored stable essential oils
US3120442A (en) 1962-10-23 1964-02-04 Freshway Products Company Natural citrus fruit aqueous essence emulsion and process of making the same
US3300320A (en) * 1962-11-19 1967-01-24 Adolf P Distelkamp Process of producing and using flavoring components of citrus fruit juices and product
US3118776A (en) 1962-12-03 1964-01-21 Ellis M Byer Production of flavor-enhanced citrus concentrates
US3353961A (en) * 1963-12-30 1967-11-21 Dominion Products Inc Stabilized flavoring concentrates
US3782972A (en) 1971-01-26 1974-01-01 Department Of Citrus Essence for enhancing the flavor of citrus juices
US3917865A (en) 1974-01-28 1975-11-04 Us Agriculture Co-distillation method for recovering volatile flavor compounds from citrus essence oils

Also Published As

Publication number Publication date
DE3112380A1 (en) 1982-10-21
DE3260343D1 (en) 1984-08-16
US4435437A (en) 1984-03-06
US4508747A (en) 1985-04-02
AU570842B2 (en) 1988-03-24
AU558191B2 (en) 1987-01-22
EP0061579A1 (en) 1982-10-06
BR8201730A (en) 1983-02-22
DE3112380C2 (en) 1985-04-11
AU5701886A (en) 1986-09-11
AU8197382A (en) 1982-10-07

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